Chloroform → HCID 13650569, compound

HRID 543410Notes

Reaction equation

HRID 543410 reaction equation
[CH2:1]([C:4]1[C:17]([OH:18])=[C:16]([CH3:19])[C:15]2[O:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:20])[C:6]=2[CH:5]=1)[CH:2]=[CH2:3].C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])[O-].[K+].[K+]>O>[OH:33][CH2:3][CH:2]1[O:18][C:17]2[C:4](=[CH:5][C:6]3[C:7](=[O:20])[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[O:14][C:15]=3[C:16]=2[CH3:19])[CH2:1]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 12529203HCID 12529203, compound

Product 1

HCID 13650569HCID 13650569, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-allyl-3-hydroxy-4-methyl-9-oxo-9H-xanthene (11 g) and chloroform (800 ml), 9.5 g of m-chloroperbenzoic acid was added and the resulting mixture was stirred at room temperature for 5 hours, followed by standing overnight. To the mixture, potassium carbonate (20 g) and water (500 ml) were added and the resulting mixture was subjected to extraction with chloroform. The chloroform layer was dried and the solvent was distilled off. The residue was recrystallized from ethanol to obtain 10 g of 2,3-dihydro-2-hydroxymethyl-11-methyl-5-oxo-5H-furo[3,2-b]xanthene. m.p. 242°-243° C. This compound gave a mass spectrum having a molecular ion peak at m/e 282.

Workup

  1. additionwas added
  2. waitby standing overnight
  3. extractionthe resulting mixture was subjected to extraction with chloroform
  4. dry with materialThe chloroform layer was dried
  5. distillationthe solvent was distilled off
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-69874d444bfc4a3cb30c79cc7934ad50
Source dataset
uspto-grants-1987_04
Patent number
US04661607

Reaction notes

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